See the Charleston of Decades Ago: An Educational (and Periodically Boozy) Tour of the Holy City

Drayton Hall

Yes, Charleston is full of brilliant restaurants and bars to try. But we’ve got a more reflective sort of trip planned for you in the charming Lowcountry.

Most visitors flock to Charleston for the food, the picturesque scenes, and the Southern charm and hospitality. But many may not realize just how rich the history is in this old town. History is an integral part of this city, manifested in the architecture, in the land, in the monuments. There’s no doubt that a foodie tour of Charleston is a priority, but there are also some incredible historic landmarks that are must-sees. Here’s our guide for the perfect Charleston weekend getaway that’ll take you back in time and immerse you in nature. And don’t worry—we didn’t forget about dinner and cocktails. 


Start your historical weekend off with a tour of Fort Sumter, one of the most important and iconic monuments in the history of the United States. In the Spring of 1861, years of tension between the North and South finally came to a head as the first shots of the Civil War were shot here. During the war, Fort Sumter served as the focal point in Charleston, but it is now a National Monument open to the public. The fort is only accessible by boat, but learning about the incredible history and being able to reflect on our past is definitely worth the trip. 

167 Raw Oysters
Oysters at 167 Raw

If you’re in the mood for a seafood dinner, look no further than 167 Raw. It’s technically an oyster bar, but this spot offers an extensive menu of everything from fresh crab claws and little neck clams to fish tacos and lobster rolls. We’re sure you’ll get your fill of the flavors of the ocean. 

The Gin Joint is the perfect spot for post-dinner drinks. They boast an ever-changing menu of innovative cocktails made with many locally sourced ingredients, classic drinks with a twist, and quick bites like house-made soft pretzels, ice cream, and beef jerky. 

Drayton Hall
Drayton Hall


Drayton Hall is the perfect place to begin your Saturday. It’s the oldest preserved plantation house in the United States that’s still open to the public. Along with being surrounded by the stunning Palladian architecture, you can stroll around the property’s picturesque landscape and gardens. Whether you’re on a 45-minute guided tour of the house, enjoying a self-guided nature walk on the property, or taking a quiet moment to reflect at Drayton Hall’s African American cemetery, the experience will be unforgettable. 

The Red Wedding at Edmund's Oast
The Red Wedding at Edmund’s Oast

Next historical stop: the Battery. Antebellum houses line the streets, making it one of the best photo opportunities in the city. During the Revolutionary War, the War of 1812, and the Civil War, the Battery served as a defensive seawall, and from the harbor, you can see Fort Sumter in the distance.

By now you’re probably craving a cold beer and we know just where to go. Edmund’s Oast is not only a brewery, but it’s also a restaurant that serves seasonal dishes and an encyclopedic bar program—a trifecta that provides the ultimate late afternoon dining experience. 

The Vendue
The Vendue Hotel

For your last night, The Rooftop Bar at The Vendue provides panoramic views of the Charleston Harbor, Waterfront Park, and more. The weekends bring a much livelier energy and the cocktails alone are enough to make you want to stop by—classic libations with a contemporary edge are their specialty. The Hibiscus Gin Fizz, Peach Mule, and Strawberry Basil Lemonade are just a few of the delectable beverages available. 

The Strawberry Basil Lemonade at The Rooftop Bar
The Strawberry Basil Lemonade at The Rooftop Bar


If you want to squeeze in one more landmark before leaving Charleston, try the Charleston City Market which has been around since the early 19th century. Home to hundreds of vendors, the market spans four whole blocks. Meats, vegetables, and fish were sold from sheds until 1841, when the current Market Hall was erected. Today, you can find art galleries, jewelry stores, sweet shops, and countless other vendors. A Charleston specialty that is still sold at the market today is sweetgrass baskets: One of the nation’s oldest handicrafts of African origin, these things were initially used as winnowing fans to separate rice seeds from its chaff, sweetgrass baskets are now considered a prized cultural souvenir. 

Charleston City Market

On your way out, stop by the old-school inspired joint, Little Jack’s Tavern, for a hearty lunch and a refreshing drink. We love the Double Tavern Burger, shrimp and farro Salad, garlic knots, pastrami on rye, and the crab roll, but your last bite of the Holy City is up to you. Make it count.